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Enantioselective synthesis of spiro[4H-pyran-3,3'-oxindole] derivatives catalyzed by cinchona alkaloid thioureas: Significant water effects on the enantioselectivity.

ABSTRACT: An efficient stereoselective three-component reaction for the synthesis of functionalized spiro[4H-pyran-3,3'-oxindole] derivatives was realized through an organocatalyzed domino Knoevenagel/Michael/cyclization reaction using a cinchonidine-derived thiourea as the catalyst. Using water as the additive was found to improve the product ee values significantly. Under the optimized conditions, the reactions between isatins, malononitrile, and 1,3-dicarbonyl compounds yield the desired spirooxindole products in good yields (71-92%) and moderate to high ee values (up to 87% ee).

SUBMITTER: Konda S

PROVIDER: S-EPMC7530948 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of spiro[4H-pyran-3,3'-oxindole] derivatives catalyzed by cinchona alkaloid thioureas: Significant water effects on the enantioselectivity.

Konda Swapna S Jakkampudi Satish S Arman Hadi D HD Zhao John C-G JC

Synthetic communications 20190814 21

An efficient stereoselective three-component reaction for the synthesis of functionalized spiro[4H-pyran-3,3'-oxindole] derivatives was realized through an organocatalyzed domino Knoevenagel/Michael/cyclization reaction using a cinchonidine-derived thiourea as the catalyst. Using water as the additive was found to improve the product ee values significantly. Under the optimized conditions, the reactions between isatins, malononitrile, and 1,3-dicarbonyl compounds yield the desired spiroox ...[more]

PMID: 33012850

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